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October 2026

  1. Annapolis Pride Parade & Festival

    Don’t miss the Annapolis Pride Parade & Festival on October 3, 2026! The parade will start in downtown Annapolis at 11:00 am, and the festival will take place at the…

    Free

  2. See Beyond Festival

    Maryland School for the Blind 3501 Taylor Avenue, Nottingham, MD, Nottingham, MD 21401, United States

    This free community event encourages people of all ages and abilities to “see beyond” through adapted activities that help everyone learn about and embrace accessibility. All visitors to the See…

  3. Lower Body Fascial Maneuvers Class

    Honey’s Farmhouse 5819 Brooks Woods Road, Lothian, 20711, United States

    Fascial Maneuvers use gentle, spiral-based movements and breath to create movement and pressure through the fascial system—helping release restrictions and restore more balanced flow throughout the body. Saturday, October 3,…

    $33

  4. Doggy Dive In

    Kenneth R. Dunn Municipal Pool at Truxtun Park 251 Pump House Road, Annapolis, 21403, United States

    🐾💦 End another pawsome summer with a splash at Dunn Municipal Pool! Bring your pup out for a tail-wagging morning of swimming and fun as we close out the pool…

    $10

  5. Maryland Renaissance Festival

    Maryland Renaissance Festival, 1821 Crownsville Rd, Annapolis, MD 21401, USA Crownsville Road 1821, Annapolis, Maryland 21401, United States

    The Maryland Renaissance Festival, a tradition for the entire family, begins its 50th season on August 29th and runs Saturdays and Sundays and Labor Day Monday through October 25th for nine…

  6. The Stable Strength & Conditioning Grand Opening

    Stable Strength & Conditioning Mitchells Chance Road 189, Edgewater, Maryland 21037, United States

    The Stable Strength & Conditioning is opening its doors on October 3 and we’d love to have you there. Join us from 8:00 am-12:00 pm for our Grand Opening with…

  7. Fall Saturdays at Ridge Grow

    Ridge Grow 244 Old Mill Bottom Rd S, Annapolis, 21409, United States

    Fall Saturdays are coming to Ridge Grow! 🍂🎃 Every Saturday Sept. 12–Oct. 31 — pumpkins, mums, fall finds, food trucks & family fun! Bring the whole family and enjoy our…

    Free

  8. Margo Price: Wild At Heart Tour

    Rams Head On Stage, 33 West St, Annapolis, MD 21401, USA West Street 33, Annapolis, Maryland 21401, United States

    Nearly a decade ago, Margo Price turned Nashville on its head with her breakthrough, beloved debut solo album, Midwest Farmer’s Daughter. Released in the throes of bro-country and before pop…

  9. Hamlet

    Classic Theatre of Maryland 1804 West Street, Suite 200, Annapolis, 21401, United States

    Experience the play that has captivated audiences for over four centuries as Classic Theatre of Maryland opens its season with Shakespeare’s greatest masterpiece. Set within the intrigue of the royal…

    $61.75 – $98.75

  10. Our Town

    The Colonial Players, 108 East St, Annapolis, MD 21401, USA East Street 108, Annapolis, Maryland 21401, United States

    Set in the small New England community of Grover’s Corners, Our Town follows the lives of the Webb and Gibbs families as they navigate love, marriage, and loss. Our Town invites us…

  11. Station 7 Terror Trail

    Davidsonville Park-and-Ride 2701 Davidsonville Road, Davidsonville, United States

    Welcome to the AVFD Station 7 Terror Trail! We are a fully volunteer-staffed fundraising event for the AVFD Station 7. Our family-friendly haunted trail has activities for everyone: The Terror…

  12. Pippin

    The Bowie Playhouse 16500 White Marsh Pk Dr, Bowie, United States

    Heir to the Frankish throne, the young prince Pippin is in search of the secret to true happiness and fulfillment. He seeks it in the glories of the battlefield, the…

    $19 – $30

  13. You’re a Good Man, Charlie Brown

    Live Arts Studio at Westfield Annapolis 2002 Annapolis Mall, Annapolis, 21401, United States

    Charlie Brown and the entire Peanuts gang explore life’s great questions as they play baseball, struggle with homework, sing songs, swoon over their crushes, and celebrate the joy of friendship.…

  14. Echoes of the Earth

    Maryland Hall 801 Chase Street, Annapolis, Maryland 21401, United States

    From the whispered stillness of Antonín Dvořák’s Bohemian landscapes to the searing emotional power of Jennifer Higdon’s Cello Concerto—brought vividly to life by Julian Schwarz—Echoes of the Earth invites you into a world where…

  15. Navy Men’s Ice Hockey vs Delaware

    Brigade Sports Complex 64 Greenbury Point Road, Annapolis, 21402, United States

    Grab a bite to eat and take in a Navy Ice Hockey Game! Match day concessions available for purchase on the second deck of the Brigade Sports Complex at Coach’s…

  16. Navy Women’s Volleyball vs Loyola Maryland

    Wesley A. Brown Field House United States Naval Academy, Annapolis, United States

    Don’t miss this Navy vs Loyola Maryland women’s volleyball game on October 2, 2026 at 6:00 pm. This event will take place at the Wesley A. Brown Field House. (DNML)

  17. Food Truck Fridays

    Anne Arundel County Farmers Market, 275 Harry S. Truman Pkwy, Annapolis, MD, 21401, United States Harry S. Truman Parkway 275, Annapolis, Maryland 21401, United States

    Check out the menus and come hungry! Food Truck Fridays in Annapolis start at 4:00 pm with great food, good vibes, and the perfect way to kick off the weekend.

  18. Featured: Michael McHenry

    Beer Farm @ Homestead Gardens 743 West Central Avenue, Davidsonville, MD 21035, United States

    Michael McHenry, a seasoned artist, injects his performances with a unique blend of soulful, sexy, and psychedelic funk-rock. His profound love for music is evident in every note he plays.…

  19. Annapolis Lower School Parent Preview Day

    Annapolis Lower School 710 Ridgely Ave, Annapolis, United States

    Come see what makes AACS a place where academic excellence and a growing relationship with Jesus Christ go hand in hand. Register here! This event will take place at the…

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